Cyclohexanone → 4-[(4-Bromophenyl)(cyclohexylidene)methyl]-3-methylphenol

Participants

Reaction Steps

To a slurry of zinc powder (1.15 g, 17.59 mmol) in THF (10 mL) was added TiCl4 (0.90 mL, 8.21 mmol) dropwise. The mixture was heated at reflux for 1 h. A mixture of cyclohexanone (0.64 mL, 6.17 mmol) and (4-bromophenyl)(4-hydroxy-2-methylphenyl)methanone (28) (0.60 g, 2.06 mmol) in THF (10 mL) was added dropwise and continued to stir at reflux for 20 min. Upon cooling, the reaction mixture was poured into a 10% aqueous K2CO3 solution. The quenched reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc. The filtrate was dried over MgSO4, filtered, and concentrated to yield 0.60 g (81%) of the compound 29. 1H NMR (400 MHz, CDCl3): δ 1.50-1.63 (m, 6H), 1.96-2.01 (m, 2H), 2.05 (s, 3H), 2.27-2.28 (m, 2H), 4.54 (s, 1H), 6.60-6.62 (m, 2H), 6.93-6.95 (m, 1H), 6.98 (d, J=8.4 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H).

Provenance & Evidence